1-acetyl-3-cyclohexen-1-ol | 82873-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetyl-3-cyclohexen-1-ol
• 英文别名: 1-(1-Hydroxycyclohex-3-en-1-yl)ethanone
• CAS: 82873-57-2
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: JUAMLRHXBNIFNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  238.4±40.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-3-cyclohexen-1-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以75%的产率得到4-hydroxy-2-cyclohexenone
  参考文献：
  名称：

  Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one asa diels-alder ketene equivalent for the synthesisof γ-hydroxycyclohexenones

  摘要：

  A short and regioselective synthesis of gamma-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the alpha-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding gamma-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00928-x
• 作为产物：
  描述：

  1-acetyl-3-cyclohexen-1-yl p-nitrobenzoate 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以99%的产率得到1-acetyl-3-cyclohexen-1-ol
  参考文献：
  名称：

  Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one asa diels-alder ketene equivalent for the synthesisof γ-hydroxycyclohexenones

  摘要：

  A short and regioselective synthesis of gamma-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the alpha-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding gamma-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00928-x

文献信息

• Catalyzed cycloaddition reactions of α-silyloxy-α,β-unsaturated ketone and aldehyde
  作者：Tadashi Sasaki、Yukio Ishibashi、Masatomi Ohno

  DOI：10.1016/s0040-4039(00)87192-0

  日期：1982.1
• Blackburn, Christopher; Childs, Ronald F.; Kennedy, Roger A., Canadian Journal of Chemistry, 1983, vol. 61, p. 1981 - 1986
  作者：Blackburn, Christopher、Childs, Ronald F.、Kennedy, Roger A.

  DOI：——

  日期：——
• SASAKI, TADASHI;ISHIBASHI, YUKIO;OHNO, MASATOMI, TETRAHEDRON LETT., 1982, 23, N 16, 1693-1696
  作者：SASAKI, TADASHI、ISHIBASHI, YUKIO、OHNO, MASATOMI

  DOI：——

  日期：——
• BLACKBURN, C.;CHILDS, R. F.;KENNEDY, R. A., CAN. J. CHEM., 1983, 61, N 9, 1981-1986
  作者：BLACKBURN, C.、CHILDS, R. F.、KENNEDY, R. A.

  DOI：——

  日期：——
• Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one asa diels-alder ketene equivalent for the synthesisof γ-hydroxycyclohexenones
  作者：Marfa E. Ochoa、Marfa S. Arias、Raul Aguilar、Francisco Delgado、Joaquin Tamariz

  DOI：10.1016/s0040-4020(99)00928-x

  日期：1999.12

  A short and regioselective synthesis of gamma-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the alpha-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding gamma-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided. (C) 1999 Elsevier Science Ltd. All rights reserved.